Wanna Bet? The 10 Craziest Wagers Ever Made By Rappers

The Bet: No money was on the line, but in September 2007, Fif said that if his album, Curtis, got outsold by Kanye West's album, Graduation, which was dropping on the same day, he'd retire from the rap game. Gambling with your gamble? Now, that's G!

The Result: Kanye easily outsold 50. Yet, last we checked, 50 is still rapping. Hmmm...Not that we're complaining, but you do know how to make good on your bets, right, Fif?

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Rapper Bet 1

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Rapper Bet 2

The Rapper: Mos Def

The Bet: In May 2009, Mos said he'd put up $1 million on MF DOOM against Lil Wayne.

The Result: Um, we're not sure if Mos quite understands how betting works. In order to "bet a million dollars on DOOM against Lil Wayne," you need to be able to quantify each side somehow so that a winner can clearly be decided. So, in essence, Mos just made this statement to try and make a point. There was no real chance of him losing a dime off of it. However, we like the sentiment and we love the idea of Mos, of all people, betting more money than 50 Cent just bet. So we'll allow it and include it on this list.

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Rapper Bet 3

The Rapper: Bow Wow

The Bet: In August 2010, he bet Game $100,000 that he could beat him in a game of Madden 2011.

The Result: Bow Weezy appeared on an episode of George Lopez Tonight a few nights later and admitted that he lost to Game—and lost bad to him. Who says playing video games all day will never get you anywhere in life? Don't tell that to Game!

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Rapper Bet 4

The Rapper: Birdman

The Bet: In February 2011, Lil Wayne's "daddy" put up $1 million on the Green Bay Packers—Weezy's favorite NFL team—to beat the Pittsburgh Steelers in the Super Bowl.

The Result: The Packers won 31-26, and Baby collected a king's ransom for having the testicular fortitude to bet against the Steelers vaunted defense. Way to trust Wayne on this one, Baby.

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Rapper Bet 5

The Rapper: Rick Ross

The Bet: In May 2011, Rick Ross met Manny Pacquiao before his bout with "Sugar" Shane Mosley and said he'd be putting a million dollars on Pacman's next fight, which turned out to be a match against Juan Manuel Marquez.

The Result: No word on whether or not the Boss actually got this bet in. But, if he did, he won! Ross has also gone on the record and said that he'll be putting up a cool $5 million on Pacquiao if and when he ever gets around to fighting Floyd Mayweather, Jr. Can't wait to see that! Maybe we can convince 50 to throw a few bucks on his boy Money May?

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Rapper Bet 6

The Rapper: John "Fatboy" Powell

The Bet: In May 2011, the little-known rapper from Illinois bet people at a party $5 that he could take a punch in the face from a girl.

The Result: He lost. And when we say he lost, we mean he lost. We'll be honest: We'd never heard of Powell, a member of some group called the Krazy Killaz, until this incident. But it's easily the craziest bet on this list. A woman by the name of Tiffany Startz eventually agreed to take Powell's bet, socked him in the face, and accidentally killed him. She's now facing reckless conduct and battery charges and he's dead. It was definitely not the way either of them planned on things going down.

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Rapper Bet 7

The Rapper: Birdman

The Bet: In June 2011, Baby put up $2 million on the Miami Heat to win the 2011 NBA Finals.

The Result: He lost. The Heat, of course, got dismantled by Dirk Nowitzki and the Dallas Mavericks in the best-of-7 series and LeBron James, Dwyane Wade, and Chris Bosh lost in their first trip to the Finals as a trio. As a result, Birdman had to force Lil Wayne to release his new album, Tha Carter IV, way ahead of schedule to pay off his gambling debt. Er, just kidding. But, wouldn't that explain a lot?

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Rapper Bet 8

The Rapper: Bow Wow

The Bet: In July 2011, for some inexplicable reason, Bow Weezy bet Kobe Bryant $1000 that he could beat him in a game of one-of-one.

The Result: Weezy got killed on the court—note to anyone else thinking about making this bet: Kobe Bryant does not take it easy on folks on the court, no matter who you are—and promptly had to pay Kobe a grand. Now that his ex-wife Vanessa just got $75 million of his money, let's hope he stored it away in a safe place for a rainy day.

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Rapper Bet 9

The Rapper: 50 Cent

The Bet: In October 2011, Fif bet Lady Gaga's social media advisor Matt Michelsen $1 million that he couldn't finish the Ironman World Championship in Hawaii as a way to try and motivate him to finish it.

The Result: Michelsen finished the Ironman race and—we're guessing/hoping—50 paid up. If not, he better holler at him now. Fif's clearly got at least an extra $500,000 laying around after last weekend.

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Rapper Bet 10

The Rapper: Birdman

The Bet: Earlier this week, the frequent gambler (this is his third appearance on this list, for those who've lost track at this point!) came out and said that he's willing to bet someone $5 million that the New England Patriots will beat the New York Giants in the Super Bowl on February 5.

The Result: TBD! To date, there have been no takers. And we don't expect there to be any takers. After all, 5 milli is a hell of a lot of money. But, wouldn't it be funny if Jay-Z called dude and put it up? Five million isn't a small sum of money, but if there's anyone who can afford to lose it, it's Jay-Z. Plus, how awesome would it be to see Blue Ivy Carter go to college courtesy of Birdman? Ha! Somebody make this happen.